


Kinktober Day 5: Double Penetration

by tiamatv



Series: Promptober 2020 [4]
Category: Supernatural
Genre: Alternate Universe - Canon Divergence, Anal Fingering, Case Fic, Castiel and Dean Winchester Need to Use Their Words, Double Penetration in Two Holes, Fuckbuddies, Gender or Sex Swap, Kinktober 2020, M/M, Plot What Plot/Porn Without Plot, Porn with Feelings, Rimming, Top Castiel/Bottom Dean Winchester, Vaginal Sex
Language: English
Status: Completed
Published: 2020-10-05
Updated: 2020-10-05
Packaged: 2021-03-07 18:14:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,986
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26852020
Author URL: https://archiveofourown.org/users/tiamatv/pseuds/tiamatv
Summary: When they catch up with Sam’s social justice crusader feminist, she looks at Dean, his Colt in hand, leather jacket with its collar flipped, like he’s the most disgusting thing she’s ever seen. He already knows this is all gonna go to hell when she screams something about “toxic masculinity.”Just before she blasts Dean in the face with something that comes in all the colors of Skittles.And glitter.
Relationships: Castiel/Dean Winchester
Series: Promptober 2020 [4]
Series URL: https://archiveofourown.org/series/1954990
Comments: 15
Kudos: 237





	Kinktober Day 5: Double Penetration

**Author's Note:**

> Vaguely season... 5-6ish? I really didn't try to fit this anywhere in continuity, but that's sort of where I'm imagining it.
> 
> Yes, there are only two people in this particular double penetration story. My brain just couldn't handle any multishipping tonight.
> 
> Sooooo I spent the entire evening writing something else rather than writing this, and then pounded (ha ha) the rest of this out in the last hour or so before I passed out. This was a probably futile effort to get it in on the correct day so I don't have to work on it tomorrow. I apologize in advance.
> 
> It is completely unbetaed, I haven't even reread it (so there may be dangling sentences at some instances) and I'm almost sure I'm going to go back at some point and rework all of the language in it. Ugh.

Dean whimpers “ _Fuck_!” in a high, throaty voice as Cas pushes into his… his… his… _her?_ Wait, fuck no. His—

Goddammit.

Okay. Back up.

Sam says, all the time, that not all witches are evil. Where’s he getting that bullshit, though, Frank L. Baum? Yeah, Dean’s always going to have to agree to disagree on that one. Just because they’re not _doing_ evil things all the time and might go to, whatever, PTA meetings now and again doesn’t mean they _aren’t_ evil.

This one wasn’t all bad, Sam insisted. Oh, yeah. All she was doing was _making guys’ balls disappear_.

How the fuck is that not _pretty fucking ‘all bad?’_

(Dean doesn’t know if everything else goes with them. He hasn’t wanted to know. He held up a finger when Sam tried to tell him. The second time Sammy opened his mouth, Dean held up his Colt.)

“They come back, though!” Sam tells him. “She’s just a… a, you know.” He stands straight in the face of the eyebrows Dean’s arching at him. “Um… according to her website, she’s… a social justice crusader. A radical feminist.” Sam almost wilts when Dean’s head tips forward in complete disbelief, but then he pushes his chin back up again. “They’re not harmed by it, not long term. I’m sure if we talk to her, we can get her to understand."

Dean stares at him. “You know how when you get kicked in the nuts, it hurts really, _really_ fucking bad for a while?” he asks. “You know, you’re rolling around on the ground and gagging and shit, and sonofabitch you kinda want to die. But by tomorrow you’re fine, just a bit of bruising or something. Right?”

“Um.” Sam blinks. “Does this happen to you often?”

“Shut up,” Dean grunts. “ _Anyway_. Would _you_ say that’s no harm, no foul, just some social justice crusader shit?”

Sam’s whole face squishes in towards his nose. “I really don’t think that’s the same thing, Dean.”

Maybe so, maybe no. Dean finds it really damned suspicious that no-one they interview is willing to tell them _how_ they got their bits back, but he’s got a sinking feeling that they’re going to find out.

When they catch up with Sam’s social justice crusader feminist, she looks at Dean, his Colt in hand, leather jacket with its collar flipped, like he’s the most disgusting thing she’s ever seen. He already knows this is all gonna go to hell when she screams something about “toxic masculinity.”

Just before she blasts Dean in the face with something that comes in all the colors of Skittles.

And glitter.

Dean’s too busy getting the glitter out of his mouth—what the fuck, _glitter,_ now he definitely knows she’s evil!—to give chase. And Sam is too busy running in from the other room, gun up and waving in the air and then coming to a screeching halt, to go after her.

But they both sure as hell notice when Dean takes one step and almost ends up stretched out on the floor from tripping over the edge of his jeans. ‘Cause something doesn’t feel right. Something really, really, really doesn’t feel right.

Sam is pale all over, and he takes one step away from Dean’s glitter-covered ass like the glitter is actually fucking herpes and not just craft herpes (shut up, Dean spent a very nice evening at the house of a kinky-ass sweetheart of a girl who, it turns out, taught second grade art). “Dean?” he asks, shaky.

Oh, yeah, for sure, Sam’s concerned _now_.

Dean’s boots flop around on his feet. He’s pretty sure he can pull himself out of them without undoing the laces. And double fuck, Dean’s looking around and realizing that his Colt feels bigger in his hand, the _room_ feels higher, and Sammy looks like a fucking shocked skyscraper.

“ _Sonofabitch_ ,” Dean snarls—and that sure as hell isn’t his voice. The noise that came out right there isn’t something that should be coming out of a guy that has already made his way through puberty. Okay, well, _fuck_.

So. That means one of two options.

Considering what the witch screamed before she hocus pocused him, Dean isn’t even all that surprised when he grabs the neckline of the shirt that’s now bagging around him and yanks it out, peering inside it. He’s kind of hoping he’ll see the skinny body and the flat chest that he had when he was twelve or thirteen, ‘cause that was the last time his voice sounded like that.

But he ain’t counting on it.

Yep. Tits.

Not big ones, either.

“ _Sonofabitch_ ,” he repeats.

Not fucking evil _his ass_.

*_*_*_*

Sam folds the scroll back up. Dean thinks his hands might be shaking. “So, uh, this says that you have to… explore… all, uh… aspects of the… uh…” Sam gulps and looks like he might successfully have kittens right here on the floor. “Feminine mysteries.”

Dean sighs and scratches the back of his head. Goddammit. Of course. “ _Right_ ,” he spits. They’ve rolled up and duct taped his jeans so they’re not dragging on the floor, and when Sam carefully mentioned that maybe Dean could borrow a pair of the witch’s shoes, Dean demonstrated that his aim with throwing things was still just as good.

“You’re, uh… taking this better than I thought.” Sam’s eyes go big and soft and gooey. “Dean, did you hit your head? Are you alright? Does this have mental—”

“Dude, if I have to take you down at the knees to punch you in the face, I will,” Dean spits.

There’s something really wrong with the fact that _that_ makes Sam look less worried. Story of Dean’s fucking life.

Dean sighs and checks for glitter between his fingers before he rubs a hand over his face. Then through his hair. At least it didn’t get any _longer._ To be honest, he just… he really does still feel like himself. Mostly. So as much as he doesn’t want to admit that it could be worse, it really _could._ “It’s not a problem, Sam,” he finally mutters.

Sam blinks at him. Clearly—very clearly—that’s not what he expected to hear. He fishmouths a couple of times, the color draining in and out of his face like one of those documentaries that Dean’s seen about octopuses.

“It’s… not?” he finally asks, warily.

“No,” Dean says, firmly. He doesn’t want to answer any questions. Especially not from his little brother. “It’s temporary, right? Like you said.”

Sam shifts uncomfortably back and forth on his heels, far enough that Dean wonders if he’s going to topple, but he pushes forward like a weeble-wobble instead. “But… Dean, um. I’m fairly certain that ‘explore the feminine mysteries’ means—‘”

Dean’s also ‘fairly fucking certain,’ there were _pictures_ on the scroll.

“I’m very goddamned aware what it means, Samuel,” Dean growls, then winces and presses a hand to the base of his throat. Okay, news flash, this throat really isn’t meant to make his voice sound like that. That hurts. “Look, I can handle it. It’ll be fine.”

“ _Dean_ …” Sam groans. “What are you going to do?”

Dean throws up his hands. His callused, _dainty_ hands. (Okay, if he were holding them he probably wouldn’t consider ‘em all that dainty, they’re callused thick and his knuckles are knobby, but they’re just _smaller_ than he’s used to seeing his own hands.) “Jeez Louise, do you need a fucking instruction manual or something? I’m gonna call Cas, alright?” he growls.

Sam relaxes so far he almost collapses in on himself. He really _does_ double over. “ _Oh_!” he comments, with a rush of breath. “Yeah.” He looks up, and his grin is relief. “Oh, that’s a good idea. Since you know he’ll answer when _you_ call. Maybe Cas can… I mean, do you think there’s something he can do to cure you?”

Dean shrugs. “Can’t hurt to ask.”

Sam nods brightly a couple of times. He looks so relieved and guilty that Dean’s pretty sure that Sam’s gonna be offering him the motel bed without the dip in it (because for some fucking reason every single double motel room has one bed with a dip in it) for months. He’s so relieved that there’s a solution that he doesn’t even question why Dean kicks him out before he calls Cas. All he says is “I’ll pick up her trail. I’ll take care of it, Dean.”

Here's the thing about Cas. He’s an angel, yeah, no harp or robes required when he’s got an angel blade and a trench coat. He’s helpful, he’s bossy, he’s kind of oblivious, he’s definitely one of Dean’s best friends—which is really fucking weird, if he thinks about it, but weird is his life.

Dean also knows that Cas is definitely, _definitely_ down to fuck.

More specifically, down to fuck Dean.

Hey, Dean promised that Cas wasn’t gonna go to his last showdown with Rafael a virgin, and, well… after that whole fiasco with the girl for hire, he realized that it had to be someone who _got it._ Not just the angel thing—mostly, that Cas was a weirdo who stared too much and who didn’t know how to offer a pretty compliment. (Sometimes Cas offered compliments to him and Sam, but they sure as fuck weren’t pretty ones and now and again Sam had had to go Googling to figure out if Cas was saying something nice to them or insulting their ancestry.)

It wasn’t gonna be Dean’s first time with a guy, even if it _had_ been kind of a while, so… well, why not? Maybe Cas wasn’t exactly the type Dean would’ve picked, if he had to, but this was about Cas, not Dean. Besides, the sex hair and the blue eyes were kind of compelling, and he smelled nice, too—sharp and bright, like lightning, nothing artificial to it. Nothing human.

The way Cas sort of lit up bright, his chin coming up and eyes going wide in a way they hadn’t for Charity or Purity or whatever she’d called herself? “Can we?” he asked, in about as little a voice as someone could get when it was that deep and that dark.

Okay, _that_ was really fucking flattering.

And it was pretty damned good, if Dean said so himself. Good enough to come back for seconds. And thirds.

After that, Dean stops counting.

What? Cas’s O-face is actually kind of adorable. He never makes comments about Dean not calling, and he never—though Dean still wasn’t sure how—so much as hints anything is happening in front of Sam. Dean’s pretty sure Cas is getting just as much out of all of this as he is, ‘cause being Heaven’s sheriff in the middle of a civil war sounds like a fucking _terrible_ job. Who can blame the guy for needing to blow off steam?

(And if now and again he does it by fucking Dean facedown into the mattress, Dean’s not exactly gonna complain.)

So yeah, not only is Dean bi as fuck (so _him,_ of all people, getting hit by the witchy is all kinds of ironic) but Dean Winchester has a lifeline to call for this kind of shit. Besides, it’s not exactly the first time Dean’s booty-called an angel—

And now he really wants to punch himself in the brain for thinking about it like that.

Dean sighs, throws his too-small hands in the air, and grunts.

(When Sam commented earlier that the sound ‘wasn’t ladylike’ Dean proved that not only could he throw something at his brother, he could definitely still hit him.)

“Cas,” Dean mutters. “ _Cas,_ buddy, look… uh… yeah, it’s me.” Does his voice sound the same to Cas over prayer-band as it does aloud? Dean realizes he doesn’t have any idea, ‘cause, well, he’s always had just _one_ voice. “It’s Dean. I know you’re the big man on campus up there right now, but—”

The happy little flutter of angel feathers—which really, to Dean, has always sounded more like a parachute popping open—announces Cas’s entrance in a flap of trenchcoat and taxes. Cas lands just a little too close, the way he always does. If Dean reached out a hand, he could boop him on the nose.

Dean just waits for Cas to say something. He just _waits_ , sneer set firmly on his lips. He originally had both hands on his hips, but then he saw how that looked in the mirror and he crossed his arms over his chest instead.

Cas looks him up and looks him down. His plush lips, just barely, tremble at the corners before they straighten again.

“You seem different. Did you get a new jacket?” he asks, politely.

Dean would punch him, but he thinks that if he broke a knuckle he’d be _really_ pissed.

“Not funny, man,” he mutters.

Cas cocks his head, like he tried to grow a sense of humor, but it’s still just a sprout. His eyebrows furrow. Dean wonders if he can see a trickle of steam coming out of his ears.

It’s so damned Cas, though, that in the end Dean can’t help but laugh.

‘Cause, well… it _is_ sort of funny, isn’t it?

When he explains, Cas doesn’t laugh. (Which is good. Just because it’s funny doesn’t mean that Dean wouldn’t kick him in the shins with Enochian-carved steel-toed boots when he’s not watching.) Cas just folds his hands in front of himself, stands straight, and looks _extremely serious,_ even for him.

And now Dean sort of can’t stop smiling.

What the fuck is his life, that he’s standing here girlified and finding an Angel of the Lord, warrior of God and all that jazz, adorable?

“I would be very honored,” Cas tells him, surprisingly gently, and… Dean doesn’t exactly know what to do with that.

Would Dean rather be himself again, cock, balls, sass and all? Sure. Is he pissed he got whammied? Yeah. But the truth is, how many guys get this chance?

Tits, though? Disappointing. Even when Cas bites and licks at them. It feels kind of good, and a little different from when Dean was a guy, but not amazing or anything. They move on from that pretty quickly. What the hell. Really overrated.

“I am not impressed,” Cas tells him.

(Dean has no idea if he should be insulted by that. He lets it go.)

Dean’s sides are ticklish, now. More than he was. That’s just annoying, but Cas dropping kisses down his flanks and stomach on his way south feels sweet and plush. Dean never really thought about how often Cas does that, but he’s doing it now. “Hey,” Dean complains, as Cas kisses his belly button.

“Hmph,” Cas grumbles, but he keeps going.

Dean would admit, he kind of was a little nervous about what the hell _this_ was gonna feel like—tits are one thing, all the _everything_ down there is… well, Dean’s had his fingers and his face in those areas enough to know that it probably fucking _is_ rocket science.

But Cas doesn’t poke around. (Dean knows better than to make the ‘buy me dinner first’ joke. The last time, Cas actually disappeared and reappeared with burgers.) Dean’s got his eyes squeezed closed, but Cas’s fingers slip in easy, no fumbling around at all. Two, right to start. His thumb rests on the outer folds, and… huh.

“Mmm,” Cas murmurs, sounding surprised and… pleased. Dean cracks open an eye and glares at him. “It’s very… wet,” he explains. “And soft. Pleasantly so.” He wiggles his fingers, and okay, that feels pretty damned good. Strange, and everything’s just… _duller_ than it feels like Dean’s used to, but not bad. Not bad at all. Dean grunts, softly.

At some points of Cas’s fingers moving, it’s like being nabbed in the prostate— _maybe_ —except it’s not. There’s no momentary sharp instant of ‘gotta pee’ that accompanies it, just an intensifying of the slick, dull pressure. It’s good, though, it’s nice. It’s not enough, but it’s… pleasant.

“Don’t get used to it,” he notes, then realizes exactly what Cas is up to when Cas carefully scissors his fingers and makes a quiet, marveling noise. He’s still looking right at Dean’s face. “Oh. I guess you, uh… don’t need to prep me,” Dean mumbles. He doesn’t know why he should feel _embarrassed_ about that, but he does.

Cas pauses. “Oh. Of course, you produce—”

“Don’t you fucking dare,” Dean spits out, but it’s sort of hard not to find this funny. In a weird, hit by rainbow glitter by a man-hater kind of way. The chuckle slips out of him before he can figure out if he wants to laugh or just kind of scream.

Cas rolls his eyes. “Why do humans make up so many terms for organs, functions, and processes, and then refuse to use any of them?” he demands.

Alright, Dean doesn’t have an answer for that. But he’s pretty relaxed by the time he gets Cas pulled on top of him—and Cas is smiling, still looking eager and excited, and looking right into Dean’s eyes. (Which might be a little weird: Dean knows where _he’d_ be looking if he was gonna fuck a girl for the first time. But he doesn’t mind. It’s just… well, it’s Cas.)

Then Cas is sinking into him. It feels… weird. Not bad. There’s no burn, no wait and ache. No _adjustment._ So, yeah, _weird_. The stretch of it is so easy, the glide of it really smooth, and—

Cas comes to a jarring stop, and Dean’s whole body jolts up against the mattress. They both pause. Cas pushes up on his arms to peer between them and looks puzzled. Dean looks, too: they’re both staring at the inch or so of Cas’s cock that’s still very clearly outside of Dean’s body.

“Oh,” Cas observes. He grinds his hips in a slow circle, like he’s trying to wedge himself deeper, and… okay, shit, that feels _really_ good, tucking and rubbing in a way that Dean is very sure doesn’t feel like anything he’s ever experienced before— “I see. It’s your cervix.”

If Dean had a boner to lose—clearly, he doesn’t—it’d be gone.

“ _Jesus fucking Christ, Cas_ ,” he hisses. “You don’t—it’s—you don’t mention—”

Even as Dean says it he realizes that makes abso-fucking-lutely no sense.

Cas blinks at him, looking adorably confused.

“Nevermind,” Dean mumbles. “Just… get on with it, okay?”

Cas frowns, and he opens his mouth, but Dean squeezes around him—it goes just right on the first go; same set of muscles as squeezing his ass, which seems like it shouldn’t work, but it does, and _holy shit_ that makes feel Cas feel thick—

Cas trails off into a groan so low Dean feels it in his ribs.

Oh, hey. Neat.

It feels… good. Great, actually. It’s like nothing Dean’s ever thought he wanted, not really, but the rhythm of it’s the same, which is kind of a relief. The way Dean wants to lift up into it is the same. When he drags a leg up Cas’s hips, the angle works even _better_ than he’s used to, no need for a pillow under his hips or anything, and—

Cas stops. He _stops_ , settling on top of Dean. The angel doesn’t sweat—Dean guesses he should find that offputting and alien, but by this point it’s actually kind of nice—but Cas gets the prettiest damned sex flush all over his face and his neck. “I want to try something,” Cas murmurs.

 _“Now?!_ ” Dean gasps, rolling his hips to trying to get him deeper _in_ , dammit.

“Yes, now. I think so. I think you’ll enjoy it.”

Well, Dean was already enjoying it a whole goddamned lot, so he grumbles. But he lets Cas pull out—not like he’d be able to stop him—and turn him over onto his hands and knees… huh. Cas wants to try doggy style? Well, Dean doesn’t have a problem with that, not at all. Kind of a surprise, though—of the two of them, _Cas_ is the one who likes missionary a lot, says he likes to watch the expressions on Dean’s face, the way Dean’s body goes ‘pliant’ under him—though sometimes he thinks that Cas is saying that just to be an asshole, ‘cause he knows that that kind of compliment makes Dean blush…

Dean freezes. On his hands and knees, he freezes.

Oh.

“Guess this’s tough for you,” he mutters, his mood soured, but he sticks his ass and his other bits up in the air anyway. “Sorry, should I, uh. Should I have asked someone else?”

Cas’s hands are wandering absently over the globes of Dean’s rear and up the narrow dip of his back when they pause. He pulls away, to Dean’s irritation. Might as well get this shit over with, right?

“Dean?” Cas asks, sounding startled and a little hurt. “What do you mean?”

Shit. Fucking shit. Dean’s big fucking mouth. Cas was already kind of on board—shouldn’t that have been enough? He shouldn’t have said anything.

Dean flops onto his back and flicks an illustrative hand down the line of his body—the tits, the soft little curves of his hips. He doesn’t try to hide his scowl.

He’s a pretty damned good-looking girl, if he says so himself. He’s not a bombshell or anything, but he’s nice-looking. He looks like an athlete—strong body, lean, not soft everywhere, but soft in a couple of good places.

But—here’s the kicker. Sure, Cas said he’d be ‘honored.’ He was seeming kind of into it, to be honest, up until that second.

But… since when has Cas shown so much as a _blink_ of interest in girls?

Guy’s as gay as angels get. Dean knew that. Hell, he ran off a girl who gets paid to make guys smile, and practically said “Oh, yes please,” when Dean so much as crooked a finger at him.

Dean didn’t really think that hard about that when he called Cas up to bat, did he. ‘Cause, well…

No, he just hadn’t thought about it _at all_. That’s on him, not Cas.

Cas frowns. “Yes?” he says, and he sounds legitimately confused now. “Is there something about…” and he just trails off, shaking his head. “I don’t understand,” he finally admits, his voice in a low gravel.

Dean sighs, and scratches roughly at the back of his head. He wants to have this talk about as much as he wants to shoot himself through the thigh. And all of a sudden this curse seems a lot less fucking amusing. “I get it, okay?” he mutters, and turns his face away. “S’easier when you don’t gotta look at…” he flicks his hand towards his chest, his face. “You know what?” He sits up and slings a leg over the bed, climbing out so fast he almost unbalances himself. “Never mind. I’ll…”

He'll what? He’ll go find someone else?

Dean has no good explanation for why that thought makes him feel kind of sick to his stomach. He looks down at his body—light pink nipples, bit of fluff between his legs with none on his thighs, lean legs and narrow hips.

He’s not bad-looking. But he’s sure as fuck not _himself_.

But Cas is looking at him from the bed, wide-eyed, now, curled in on himself with one knee pulled up to his chest, and clearly the poor guy has no fucking idea what the hell just happened here.

Dean blows out a breath that runs hissing through his teeth. “I get it, Cas. S’okay. I appreciate you being willing to, y’know, take one for the team or give one for the team or… whatever. You don’t have to force things. I can find someone else.”

Jesus. Saying that makes it real, and this time, there’s no mistaking the twist of nausea in Dean’s gut.

Yeah, he’s bi. Yeah, he’s been with guys, sure—truck stop restrooms, now and again a bar where no-one’s looking too closely in the bathrooms. Dean hasn’t done that in years, because it never made him feel as good as the feelings his body gave him for it. But he could probably do it again. If he had to.

But he wasn’t thinking of that when he told Sam he had it covered. He hadn’t thought of making himself vulnerable when Dean, of all people, knows that men can be assholes, especially to a girl who looks like she’s out to play. He knows what can happen; he knows that no-one looks at Dean Winchester and sees a victim, no matter what anyone says about his pretty eyes and soft lips. But no-one’s gonna look at him and see Dean Winchester now, even if he _is_ still tall and with muscles in the right places.

(He stands by what he thought of the witch: _evil_.)

But, no, none of that had occurred to Dean. He thought—right then, right there, looking side by side with his brother at the stupid fucking _sex_ _diagrams_ written on a papyrus scroll, “ _Hey… this might be kind of fun, Cas might get a kick out of it.”_

Dean hadn’t been all that worried, ‘cause, right away, yeah, he’d thought of _Cas_. Dean’s gay angel in a trench coat and a boxy suit, with the big blue eyes, the shy tiny smile and the eager, callused hands that definitely don’t belong to a tax accountant.

Goddammit, Dean is a real fucking idiot.

Cas’s shoulders are hauled in high, now, his chin tucked, and it’s been a long time since Dean looked at him and thought, _huh. He’s little._ “What did I do wrong?” he asks, sounding frustrated.

“Nothing, Cas. _Nothing_ ,” Dean spits, his hands in fists. But Cas is looking at him now like Dean’s got an angel blade to his throat, and Dean’s not exactly being fair here.

Does he feel like being fair? He really, really doesn’t.

But he, of all people, knows just _how_ unfair it is to blame Cas for not wanting to look at him while they fuck when he’s _not Cas’s type_ anymore. The irony of it is pretty damned staggering, if he says so himself.

Dean’s shoulders sag. “Not your fault you’re not into chicks, okay, Cas? You shoulda just said.”

But Cas is looking at him like he’s watching Dean’s marbles rolling across the floor in all directions and he’s not sure which of them he’s supposed to catch up to first.

“Are you referring to your vessel?” he asks, sitting back on his heels. He’s still naked and has no fucks to give about that, so Dean can’t exactly be bothered to cover himself up, either. Even though he wants to, now. Wants to wrap himself back in jeans and flannel and boots, and it doesn’t matter how badly they fit, they’ll make him feel more like _him_.

“Humans don’t have vessels, Cas,” he answers, tiredly. “You know that.”

Cas frowns. “Most don’t—of course. But what do you call your situation, Dean? The body you’re currently wearing temporarily contains you, but you don’t consider it yours. You—the nature of you—are unchanged. Isn’t that what a vessel _is_?”

Huh.

Cas squints at him. Finally, he shakes his head. “You think I don’t want to have sex with you because your body is _different?_ ” And he sounds so genuinely weirded out by the idea that Dean actually looks him in the eye. The sincerity there when Cas stares back at Dean is, well… it’s angelic, is what it is. “Why... humans are so strange," he complains. "I have intercourse with your body, Dean. But I desire _you_. Those are different things. Don’t get them confused.”

Dean thinks he might have something smart to say to that, ordinarily.

(That’s a lie. He wouldn’t.)

Dean would like to think the fact that, once his knees are steady again, he strides over to Cas, grabs him by the hair on the back of his head, bends him back and sticks his tongue down his throat has something to do with the fact that they stopped pretty much halfway through fucking.

(That’s also a lie.)

“You’re not going?” It’s not a plea; nothing is, in that harsh rumble—Dean is very sure that angels don’t know how to beg, though he’s been looking forward to finding out if he can make Castiel break that rule. But Cas’s hand is resting on his hip a little too firmly, and the fingerprints he’s leaving on Dean’s skin ache in the most damned pleasant way.

“How come you wanted me to flip over?” Dean asks. He doesn’t answer the question.

“You’ve taught me that different positions have different benefits,” Cas answers, without blinking. “I think I still prefer the other way, as I prefer to look into your eyes, but you seem to enjoy deep penetration, and I believe the angle would be better for that.”

Oh.

Well, shit.

Dean knows his smile is a little stupid, and maybe a little crazed, when he runs the fingers of one hand roughly through Cas’s hair. “You know what?”

“Hm?”

“You’re a pretty good angel.”

Cas scowls at him. “I am a _terrible_ angel, but I think I am finding that enjoyable,” he pronounces, and dammit, for that, Dean kisses him again.

By the time Dean’s on his hands and knees again, they’re both more relaxed and, well, maybe a bit happy to be there. (Okay, okay. Dean can feel that he’s wet down there, after what was probably an hour of kissing and lazy making out. A little puffy. He’s not sure he likes the feeling, but he’s not mad about it. Maybe the boobs aren’t so bad, but Cas kissing down his neck seemed to do more than any fiddling with his nipples.)

Cas spreads him open and pushes one long lick up him—all the way up, his tongue skirting and dipping into Dean’s hole—huh, that’s nice, dancing in and out between all the folds. But he keeps going, following the stretch of skin upwards towards his ass—it almost feels like his tongue’s moving too fast, with no balls in the way—and then… Dean’s _other_ hole.

But that’s where he spends a little attention. That’s where the tip of his tongue flicks and plays, running over the little ridges and creases of Dean’s pucker.

The noise Dean makes is thin and high-pitched. Okay, that, _that_ feels exactly the same. Except it’s not the _only_ part of him now that clenches empty and wet, wanting more, when Cas lifts his tongue away.

“Okay, what’re you doing?” Dean blurts out, before he realizes that Cas is probably going to answer, and after the first time, Dean doesn’t want to hear a factual definition of rimming ever again. But still, what’s he _doing?_ They’re all pretty sure that this is going to require good old penis-in-vag motion-of-the-ocean stuff.

“Hmm,” Cas comments, with interest. “You’re still sensitive here. I thought so.” He leans in and nuzzles between Dean’s cheeks; maybe Dean’s skin is thinner, or something, because the delicate rasp of Cas’s scruff on his ass doesn’t normally make him want to jackknife his way up the bed _and_ press into his face at the same time.

But Cas doesn’t stop. He keeps licking him—that familiar roll of his tongue, the way he darts it in and out and in and out in teasing little flutters, and Dean’s body _knows_ this. Cas has not a single human hangup about rimming, which is maybe why he’s so _good_ at it. It’s a familiar kind of good, though, so Dean almost keels right over onto his face when Cas’s hand glides up his thigh and two fingers fill him up in his _other_ hole, and—ah, fuck!

That’s definitely not familiar.

It's so easy, though. Open and wet, and the slosh of them in him is obscene.

“C’mon, more,” Dean gasps. And then “Oh, _yeah_ ,” when Cas pulls himself back up onto his knees and shoves himself back home with a grunt. His cock goes in easy and all the way, now, this position’s good for that, his hips hitting Dean’s thighs and his ass with a smack. He’s not _moving_ , though, he’s not giving Dean friction along with depth, and Dean has no idea why the fuck Cas is holding back—he’s so hard Dean can feel him bobbing inside him, which he’s _always_ liked—

Until he feels Cas’s hand on his ass. Until he feels two wet fingers press against the hole that’s _not_ filled and hold there, dipping tiny little vibrations along his rim. Like an invitation.

Holy shit.

Dean’s severely, _severely_ underestimated just how long Cas has been watching humanity do the dirty.

“Yes?” Cas asks, low and rumbly and eager. “I thought… you’re more accustomed to—"

“ _Fuck_ , fuck, yes,” Dean groans, and Cas presses in with his fingers and fills him up in both holes.

Cas is right, he’s more ‘accustomed to,’ and that’s _good._ That’s really good, the little ache and burn of it is weirdly grounding, and all of a sudden Dean feels more like _himself_ than he has since he got hit in the face with evil Skittles.

But it’s not the same. It’s more. It’s familiar, and it’s not, and the combination is goddamned _electric._

It takes a hot minute before they work up to a really good rhythm, and Dean’s enjoying every damned heartbeat of the experimentation. He already knew he liked being fucked up the ass, nothing wrong with that, but the way Cas is alternating his fingers and the motion of his cock is leaving Dean with his body not knowing which it wants to push towards. There’s more drag and more _pressure_ where he’s got his fingers, but he’s just _bigger_ elsewhere, and the feel of being filled up both ways is really, really fucking satisfying.

The climb’s slow. It’s really damned slow, what the fuck. But Cas has one hand braced on the small of Dean’s back like he’s got no doubt at all that Dean’s body, smaller though it is, can take it, take his weight along with the pressure and the _fill_. And he doesn’t seem like he’s in any rush at all.

When Cas gives him just one more finger, the stretch of it should feel completely familiar, easy even—this is about where they go. But it’s not, not when Dean’s already crammed full, so fucking intense. When he curves them—carefully—Dean knows he hasn’t got a prostate to press on, but it sort of _shifts_ everything delicately inside him as Cas thrusts—

The orgasm rolls up towards him and crashes in.

Dean’s had a lot of ‘em in his life—he’s not ashamed to admit it. He’s had quick little ones that were more like a snack than a meal, he’s had ones that kicked him in the ass and left him strung out and gasping. He _likes_ coming. Who doesn’t?

For the first time in his life Dean gets why it’s called the _Big_ O.

He doesn’t have a fucking point of comparison. He doesn’t have a dick for come to shoot out of, so there’s no sense of _flow_ , nothing leaving him. It’s not like it’s being punched or yanked out of him, there and then gone, ‘cause a punch doesn’t _last._ Instead, after the pleasure breaks, it just kind of whirlpools around in his pelvis, pushing and pulling, pushing and pulling, not going anywhere—but ramping in spasms as Dean’s back arches and his breath tears out of him in heaving gasps. But Cas, bless his feathers, just plain doesn’t _stop_ fucking in and out of him.

The fingers in his ass slide out first, but Cas is still filling him up the other way, still rocking, though he’s starting to slow down. It doesn’t feel achy and clenched-up and just a little weird, though, the way it normally does when the sex-high’s starting to wear off and something’s still up Dean’s ass.

It feels _good_. It feels full, but not uncomfortable, and when Cas slips inside him a bit—

Dean reaches back and clutches at Cas’s thigh hard enough to feel the scrape of his nails against Cas’s skin when Cas tries to pull out.

“Don’t stop,” Dean slurs. He can—he thinks, maybe—

“What?” Cas murmurs. “But Dean, you’ve already—”

“I know, _I know_ , don’t fucking _stop_ , Cas!” he groans. He’s not even sure he _could_ explain why if the bossy angel decided that he wants more of an explanation.

Mercifully, Cas doesn’t.

The second one rolls up slower, more like little lapping waves on his feet than one crashing over his head. He can barely keep himself up anymore, barely brace against Cas’s firm thrusts against him, but he holds where he is, balanced on his elbows, because he doesn’t want Cas to stop. The shivers arch his back, and it’s fucking _delicious_ is what it is—slow and easy, this time, and it feels like he doesn’t stop quivering for like an hour. He might have been sobbing dry, facedown and twisting after the third rush of whatever the fuck that was, but he doesn’t want to twist away in oversensitivity the way he normally does when he’s all done.

He vaguely registers that Cas comes, somewhere in the middle of that, but he doesn’t pull out—just keeps on fucking slowly in and out of Dean’s… yeah, he can say it, Dean’s pussy, and the thick wet noises of both of their wet all over the place would make Dean blush if he had any more fucks to give.

Cas molds over him, and kisses between Dean’s shoulder blades. But Dean’s little angel doesn’t pull out.

(Dean really likes that he doesn’t, this time.)

He’s also kind of liking that when he looks down absently between his arms, the tits are gone. Huh.

Dean never thought he’d say this about a pair of breasts, but good fucking riddance.

“Think it’s working,” he murmurs. Not all the way, though, not yet, ‘cause Cas is _definitely_ still tucked into him down below. The feel of him slipping out, like he heard what Dean’s thinking, is so easy; Dean grimaces a little as come trickles down the insides of both of his thighs.

“Are you up for more?” Cas whispers, and presses his thumb against Dean’s pucker. The lube hasn’t dried on it yet—and that’s not just lube, now, that’s probably some of Cas’s come, too. The tip of his thumb nudges in easily. “I would like to compare how you feel around me… here.” He rubs a tantalizing little circle, tugging at Dean’s rim.

Oh, damn.

Well, he knew Cas liked sex. And Cas _definitely_ likes it past the point where Dean’s not up for it anymore, they both know that, but Cas normally doesn’t push for more.

Dean checks in with his own body as he sits up and turns, stretching. He’s a little tired. His taint—it’s probably not called that in this situation; Dean doesn’t care—and thighs and ass are covered with wet and spunk.

But he’s not sore. He’s not on the verge of _death,_ the way he should be at his age with two orgasms one after another under his belt. Hell, he thinks maybe…

“Still up for one more, huh, Cas?” Dean grins at him. And drops a kiss on his lips.

‘Cause he can. Just ‘cause he can.

“With you, yes.” Cas licks his lips. His eyes are hopeful, and he shifts in his position sitting back on his heels. “You on top of me,” he says. “Your back to me. I would like to be in your rear, and put my fingers inside your vagina, this time. Or stimulate your clitoris, since you don’t have a prostate.” He cocks his head and looks inquisitive. “Since we have the opportunity. Do you think you’d like that?”

“’Would I like that.’ Do I look like an idiot?” Dean mutters, and crawls forward into his angel’s lap. He settles in; Cas’s arms loop around his waist. He can’t even be bothered to comment on Cas’s terminology. They’ll work on that another time.

“No. You look very pretty,” Cas tells him, lowering his head so he can make sure that he’s looking Dean in the eyes—so sweet and immensely loyal. Dean wishes he could blame his current girliness on the fact that his chest flutters like it’s the Impala and pigeons have gotten inside. "Your soul is glorious."

Except Cas says that precise thing even when Dean hasn’t got tits at all, and Dean still has that same damned reaction.

The reaction he has to Cas, very carefully and with the tips of his fingers, rubbing little circles around his wet clit, though? Holy _fuck_.

Dean’s almost disappointed when a few minutes later it’s clear that things are going back to the status quo.

(Almost.)

But it’s definitely Dean’s cock that Cas has got cupped in his hand now, thick in Cas’s hand as if Dean didn’t already have one orgasm under his belt, much less two. But Cas is still moaning and stroking him like this is the best goddamned thing he’s ever experienced, hunched at Dean's back with his chin over Dean's shoulder, watching. Dean wasn’t sure if everything from the past few hours would catch up to him once he had _his_ body back, but he can already feel the more familiar pressure and tug building deep, his balls pulling tight as Cas thrusts in and out of him, rocking slow and steady.

Yep. Dean’s gotta write this witch a thank-you card.

But he’s got a terrible angel to kiss stupid, first.

~fin~

**Author's Note:**

> Please don't judge me too harshly; this was rush writing. I swear I will clean it up at some point.
> 
> Also: please stop letting me delude myself into thinking the Kinktober fills will be 'quick little smutty things.'


End file.
